


A Night In Anguilla

by roryheadmav



Series: The (Mis)Adventures of Pirate Tom and British Navy Captain Chris [2]
Category: Alternative Universe - Fandom, Real Person Fiction, hiddlesworth - Fandom
Genre: Crossdressing, Hiddlesworth, M/M, Pirate AU, corsets, hiddlesworth au
Language: English
Status: Completed
Published: 2014-03-23
Updated: 2014-03-23
Packaged: 2018-01-16 19:19:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,027
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1358917
Author URL: https://archiveofourown.org/users/roryheadmav/pseuds/roryheadmav
Summary: <blockquote class="userstuff">
              <p>Captain Tom Hiddleston has an impromptu evening with the notorious pirate, Blackbeard.</p>
            </blockquote>





	A Night In Anguilla

**Author's Note:**

> I ended up writing this instead of doing work. I put the blame for this exclusively on Hiddleston and co. singing that darned pirate song in "The Pirate Fairy". For those of you who are asking me for more Pirate! Tom, you can thank "The Frigate That Flies" for this naughty story. :p

**A NIGHT IN ANGUILLA**

**Copyright March 24, 2014 By Rory**

 

Captain Tom Hiddleston whistled as he merrily walked along the wharf of Anguilla, heading for his ship, the Prancing Joey. In truth, he should not be so relaxed at all, his guards lowered completely, considering that the West Indies were the operating grounds of that notorious pirate, Blackbeard. In fact, his first mate earlier informed him that there were reports that Edward Teach's ship, Queen Anne's Revenge, was docked in nearby Crab Island.

 

But, Tom couldn't care less. The Prancing Joey was more than capable of dealing with Queen Anne's Revenge, his frigate being equipped with 46 cannons, 4 cannons more than Blackbeard's ship. Besides, it delighted him to no end to outwit both the pirate and the British Navy. He knew that Teach was practically gnashing his teeth that Tom and his crew had looted the Dancing Elsa, which was his intended target. Oh, he had heard of the things that Blackbeard wanted to do to him, some of which surprised him, given that he knew the pirate to be a womanizer and most definitely not a lover of boys and men. Still, Tom had to make a small concession in the event that Blackbeard does make good on his threat of capturing him and making him his whore.

 

The young pirate could not help but sigh wistfully at the pleasant memory of Captain Christopher Hemsworth. What a handsome hunk of a man he was! The poor captain never knew that Tom recognized him instantly; that was how good his information sources in British military circles were. While Tom and his men had made off with the Dancing Elsa's treasures, Hemsworth probably never realized that he had taken a more precious prize in return.

 

"It was a good exchange," Tom mused, a small smile curving up the corners of his lips. "Better that a fine, gallant English officer popped my cherry first than a creepy old pirate like Teach."

 

Tom never saw the dark figure that was tailing him in the shadows. As he turned the corner, something hit him in the back of the head and he dropped onto the floorboards of the pier.

 

When the young pirate woke up, he was having difficulty breathing. At first, he thought he was being strangled, but he soon realized that the constriction was situated around his belly. Grimacing, Tom gingerly sat up to find himself lying in a spacious bunk. When he looked down at himself though, his blue gray eyes grew as round as plates.

 

Tom was wearing a beautiful, off-shoulder, royal blue silk gown adorned with frills and ribbons. The top of the bodice was cut very low so that it hung a few inches below his shoulders. He tugged the neckline forward in order to peer down. Sure enough, he was wearing a fine whalebone corset on top of a very thin shift. The corset itself was pushing his chest upwards, giving his upper body a woman's figure and small breasts. In fact, such was the design of the constricting undergarment that his nipples were peeking, taut and tight, on top of the gown itself.

 

It was then that Tom heard heavy breathing. Scowling at the shadows, he declared, "I can hear you panting. If you're going to fuck me, you pervert, have done with it now."

 

Somehow, it did not surprise Tom to see Edward Teach himself emerge from the darkness, looking downright fierce-looking and disreputable with his thick and scraggly black beard.

 

The young pirate laughed and lay back; his upper body supported by his upper arms and bent elbows behind. "Well, well, Edward! It seems you finally have me where you want me."

 

"Aye, indeed, I do," Teach replied, his dark eyes gazing down at Tom's slender form. "Who'd ever thought you'd make a mighty fine woman, eh, Hiddleston?"

 

"Well, I've still got my manly parts underneath my gown," Tom helpfully pointed out. "Are you sure you want to spoil the illusion?"

 

"There's always a first time for everything."

 

"True, but, unfortunately for you, it won't be a first time for me. Alas!"

 

"Aye. I heard about Hemsworth's popping your cherry. I had been hoping that I would be the one to accomplish the deed. But, I've had whores before. And, besides, I hear that boys like you, unlike women, tend to regain their tightness. So it would still be like fucking a virgin."

 

Tom exhaled heavily as he flopped back on the bed. He pulled the gown up to his thighs and spread his long legs before extending his arms above his head.

 

"Have your way with me then," he replied in resignation, although there was an amused tone in his voice. "Shall I fight and struggle, like a virgin protecting her honor?"

 

Teach ripped off his shirt, revealing the broad expanse of his chest and his tight, washboard belly. "You might want to scream too," he added, grinning.

 

Truth to tell, Tom did struggle at first; in his eagerness to have him, Blackbeard was very rough with him, leaving dark bruises on his pale skin, both clothed and bared. He nearly kicked the pirate in the balls when Teach bit down on his nipple. Instead, Blackbeard pressed his knee down while raising the other leg onto his shoulder. Suckling upon Tom's abused tit, Blackbeard pushed forward, driving his cock hard and deep into that velvet heat, without any lubrication or preparations.

 

"Bastard!" Tom hissed at that sudden penetration. "Is that the best you can do? Hemsworth rode me better than you do."

 

"So, you want me to give you a good ride, eh," Blackbeard mumbled, his voice sending chilling vibrations coursing through the younger pirate's breast.

 

Tom cried out as Teach pounded inside the younger man in a hard, relentless pace. Not only did Tom's body rock with the pirate's fierce motions; it seemed as if the ship itself was rocking to its master's frenzied thrusts. His hands reached up and clung to the supports of the book shelf above him while he wrapped his legs around Blackbeard's waist. There was a deep shudder, and the pirate gushed molten heat inside his body.

 

"Is that all?" Tom whined, a luscious pout on his lips.

 

Teach glared down at him, his blue eyes reflecting his surprise and a small measure of exasperation and irritation. "If 'tis more you want, I'll be happy to oblige you."

 

"Uhm, you might want to take this off first," Tom gestured to the corset. "I think your big hands and beefy arms can mold my body to the more feminine shape that you desire."

 

The pirate seized the hem of the gown and pulled it up and over Tom's head. His blunt fingers next removed the ties and ripped the stays off, causing Tom to heave a sigh of relief. Tom unlaced the shift, letting one sleeve dip down his shoulder, baring his left chest. With his left hand, he reached for Teach's cock and began stroking it to hardness.

 

"Now that is much better," he exclaimed, relieved, and he leaned down and took the older pirate's cock inside his mouth in gratitude.

 

Blackbeard let out a choking noise, his fingers digging into the curls of Tom's blond mane. Pleased at the reaction that he was drawing from the pirate, he let his throat squeeze around the tight shaft, sucking it in while his tongue flicked along its length and teased the sensitive foreskin. Withdrawing for a moment, he licked the come that oozed from the slit. Tom expertly brought Teach on the verge of coming. But before the pirate could spill down his throat, he clamped his right hand around the base of Teach's cock and balls. Grinning wickedly, Tom slid up against the pirate's thighs, straddling them between his knees. With a sigh, he sank down upon Blackbeard's massive erection, taking it in to the hilt.

 

Teach laid his hands over Tom's hips, lifting the younger man up and down, impaling him repeatedly upon his cock. For his part, Tom ground his body against Blackbeard, his own erection caught in the friction of their pressed bodies. He even dug his fingers through Teach's beard, unaware that the scraggly facial hair was coming lose with every tug.

 

"God, I'm coming, Edward! I'm coming!" Tom panted, his eyes rolling up in his head as he climaxed all over the pirate's belly.

 

Even when Tom had fallen weary and limp in his arms, Teach did not relent in his thrusts. When he came, it was in one devastating explosion which filled the younger man's body to overflowing. Still, Blackbeard could not get enough of this beautiful young pirate's body and he took him again and again throughout the night.

 

The sun was high up in the sky when Blackbeard awoke. He never noticed that his fake beard was already hanging by its string down his neck. He was about to get up, when there was a painful tug around his cock. He gaped down in horror to find his erection and testicles bound securely by an iron manacle to which was attached a long chain secured to the book shelf above him. His cock was bent by the chain in such an awkward angle that it would take careful maneuvering on his part to simply sit up.

 

His blue eyes narrowed, seeing Tom now fully dressed once more, although he chose not to wear his long coat. Instead of his shirt, he had on the shift which he was stretching in front of him so that the fabric would not rub against his sore nipples. Even the ties of his trousers were loosened. Realizing, however, that he was probably on board a vessel that he should not be on, he pulled on the gown for good measure.

 

"What's the meaning of this?" Blackbeard demanded.

 

"You know, I was going to ask you the same thing myself, Edward…" Tom paused. "…Or should I say… ** _Christopher_**."

 

The British Navy captain's jaw dropped. How could Hiddleston have seen through his disguise? "How did you know it was me?"

 

" ** _PUHLEEZE!_** Blackbeard smells like burned hair because he always sets his beard on fire in order to intimidate the enemy. And another thing, I've had your fucking cock in my arse! I've memorized the look and feel of the damned thing…especially when it's inside my ass!"

 

Christopher could not help smiling smugly. "I take it you like my cock then, since you remember it with such obvious fondness."

 

Tom glowered back, although a similar smile was threatening to curl up his lips as well. "I could say the same about you. You like my ass so much you would even disguise yourself as Blackbeard to get your cock inside it again. Edward will probably be insulted if he hears about this. And, I promise you, he most definitely will."

 

"I guess I cannot tell you that you are under arrest on orders of the Queen."

 

"No, you're not in the position to do so."

 

"Well, you can't blame a man for trying."

 

Tom exhaled in mild exasperation. "Christopher, next time, if you want a free fuck from me, just leave a message at any of my favorite haunts. I'll be more than happy to oblige you rather than have you go to all this trouble."

 

Christopher crossed his arms behind his head and grinned. "It's the thrill of the chase, my dear. The thrill of the chase."

 

"You'll have to do better than this."

 

"Oh, I promise I'll do better." He waved his hand to his chained cock. "Now, how about you give me the key for this?"

 

"It's under the mattress at the foot of the bunk," Tom pointed to the spot, too far for the British captain to reach. "I thought I'd give myself a head start while you…" He waggled at the figure lying on the bed. "…Sort out your predicament."

 

Christopher thrust out his lower lip in a childish pout. "You are most cruel to me, Captain Hiddleston."

 

"Just giving you your just desserts, Captain Hemsworth," Tom replied as he ran out of the room, laughing.

 


End file.
